CA2075622A1 - Technologie de transvinylation assistee par un milieu azeotropique - Google Patents

Technologie de transvinylation assistee par un milieu azeotropique

Info

Publication number: CA2075622A1
Authority: CA; Canada
Prior art keywords: acid; vinyl; derivative; bronsted acid; alkenyl
Prior art date: 1990-11-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002075622A

Other languages

English (en)

Inventor

Morteza Mokhtarzadeth

Rex E. Murray

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Chemicals and Plastics Technology LLC

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-11-30

Filing date

1991-11-27

Publication date

1992-05-31

1991-11-27 Application filed by Individual filed Critical Individual

1992-05-31 Publication of CA2075622A1 publication Critical patent/CA2075622A1/fr

Status Abandoned legal-status Critical Current

Links

238000005516 engineering process Methods 0.000 title description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 135
239000007848 Bronsted acid Substances 0.000 claims abstract description 127
238000000034 method Methods 0.000 claims abstract description 64
230000008569 process Effects 0.000 claims abstract description 59
238000006243 chemical reaction Methods 0.000 claims abstract description 58
238000010533 azeotropic distillation Methods 0.000 claims abstract description 41
238000000926 separation method Methods 0.000 claims abstract description 41
239000011541 reaction mixture Substances 0.000 claims abstract description 29
238000002360 preparation method Methods 0.000 claims abstract description 19
239000000047 product Substances 0.000 claims description 131
239000002253 acid Substances 0.000 claims description 119
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 89
239000003795 chemical substances by application Substances 0.000 claims description 76
229920002554 vinyl polymer Polymers 0.000 claims description 66
238000009835 boiling Methods 0.000 claims description 59
238000004821 distillation Methods 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 45
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 32
239000003054 catalyst Substances 0.000 claims description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
-1 aroxy Chemical group 0.000 claims description 26
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 16
YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 claims description 15
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 13
IYNRVIKPUTZSOR-HWKANZROSA-N ethenyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC=C IYNRVIKPUTZSOR-HWKANZROSA-N 0.000 claims description 13
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 13
229920001567 vinyl ester resin Polymers 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 8
BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 claims description 8
235000019260 propionic acid Nutrition 0.000 claims description 8
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 8
229910052707 ruthenium Inorganic materials 0.000 claims description 8
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 8
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
125000003368 amide group Chemical group 0.000 claims description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
229950010765 pivalate Drugs 0.000 claims description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 claims description 3
LYJHVEDILOKZCG-UHFFFAOYSA-N Allyl benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1 LYJHVEDILOKZCG-UHFFFAOYSA-N 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 claims description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
150000005215 alkyl ethers Chemical class 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 3
238000005191 phase separation Methods 0.000 claims description 3
UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 claims description 3
JSDZSLGMRRSAHD-UHFFFAOYSA-N 3-methylbutan-2-ylcyclopropane Chemical compound CC(C)C(C)C1CC1 JSDZSLGMRRSAHD-UHFFFAOYSA-N 0.000 claims description 2
FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 0.000 claims description 2
GVVKBARIYRBZHC-UHFFFAOYSA-N prop-2-enyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC=C GVVKBARIYRBZHC-UHFFFAOYSA-N 0.000 claims description 2
FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 2
QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims description 2
KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 claims description 2
229940005605 valeric acid Drugs 0.000 claims 2
PIGJZPZYWKFDBR-UHFFFAOYSA-N 2,5-dimethyl-1-(4-methylpyridin-2-yl)pyrrole-3-carbaldehyde Chemical compound CC1=CC(C=O)=C(C)N1C1=CC(C)=CC=N1 PIGJZPZYWKFDBR-UHFFFAOYSA-N 0.000 claims 1
XCOWGEAIBVSRDR-UHFFFAOYSA-N 2-methylprop-2-enyl propanoate Chemical compound CCC(=O)OCC(C)=C XCOWGEAIBVSRDR-UHFFFAOYSA-N 0.000 claims 1
238000011084 recovery Methods 0.000 abstract description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
150000002500 ions Chemical class 0.000 description 16
239000012071 phase Substances 0.000 description 11
239000000376 reactant Substances 0.000 description 11
150000007513 acids Chemical class 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000004508 fractional distillation Methods 0.000 description 6
239000007789 gas Substances 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
238000004817 gas chromatography Methods 0.000 description 4
229950000688 phenothiazine Drugs 0.000 description 4
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
239000000178 monomer Substances 0.000 description 3
SAMJGBVVQUEMGC-UHFFFAOYSA-N 1-ethenoxy-2-(2-ethenoxyethoxy)ethane Chemical compound C=COCCOCCOC=C SAMJGBVVQUEMGC-UHFFFAOYSA-N 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
239000002699 waste material Substances 0.000 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
UNMYKPSSIFZORM-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)butane Chemical compound CCCCOCCOC=C UNMYKPSSIFZORM-UHFFFAOYSA-N 0.000 description 1
GZHKEFMXFNGIDG-UHFFFAOYSA-N 1-(2-ethenoxyethylsulfanyl)butane Chemical compound CCCCSCCOC=C GZHKEFMXFNGIDG-UHFFFAOYSA-N 0.000 description 1
OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 1
BQCXFGVWPFXMKD-UHFFFAOYSA-N 2,2-dimethylpropanoic acid;ethenyl acetate Chemical compound CC(=O)OC=C.CC(C)(C)C(O)=O BQCXFGVWPFXMKD-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
MKUHGTBLBQBKBC-UHFFFAOYSA-N 2-ethenoxyethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCOC=C MKUHGTBLBQBKBC-UHFFFAOYSA-N 0.000 description 1
RLJPTOIWHAUUBO-UHFFFAOYSA-N 2-ethenoxyethyl acetate Chemical compound CC(=O)OCCOC=C RLJPTOIWHAUUBO-UHFFFAOYSA-N 0.000 description 1
GNUGVECARVKIPH-UHFFFAOYSA-N 2-ethenoxypropane Chemical compound CC(C)OC=C GNUGVECARVKIPH-UHFFFAOYSA-N 0.000 description 1
YMLMPWTWWZJGAZ-UHFFFAOYSA-N 2-hydroxyethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCO YMLMPWTWWZJGAZ-UHFFFAOYSA-N 0.000 description 1
DSSAWHFZNWVJEC-UHFFFAOYSA-N 3-(ethenoxymethyl)heptane Chemical compound CCCCC(CC)COC=C DSSAWHFZNWVJEC-UHFFFAOYSA-N 0.000 description 1
ZXABMDQSAABDMG-UHFFFAOYSA-N 3-ethenoxyprop-1-ene Chemical compound C=CCOC=C ZXABMDQSAABDMG-UHFFFAOYSA-N 0.000 description 1
OJXVWULQHYTXRF-UHFFFAOYSA-N 3-ethenoxypropan-1-ol Chemical compound OCCCOC=C OJXVWULQHYTXRF-UHFFFAOYSA-N 0.000 description 1
VUEZBQJWLDBIDE-UHFFFAOYSA-N 3-ethenyl-1,3-oxazolidin-2-one Chemical compound C=CN1CCOC1=O VUEZBQJWLDBIDE-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
DDKRLVWFGBPWIO-UHFFFAOYSA-N C(C(C)(C)C)(=O)OC=C.C(=C)N1C(CCC1)=O.N1C(CCC1)=O Chemical compound C(C(C)(C)C)(=O)OC=C.C(=C)N1C(CCC1)=O.N1C(CCC1)=O DDKRLVWFGBPWIO-UHFFFAOYSA-N 0.000 description 1
XVLFFFFFDLZPEH-UHFFFAOYSA-N C(C=C)(=O)O.C(C=C)(=O)OCC(C=C)(O)CCO Chemical compound C(C=C)(=O)O.C(C=C)(=O)OCC(C=C)(O)CCO XVLFFFFFDLZPEH-UHFFFAOYSA-N 0.000 description 1
IOVZXONIQGYGEF-UHFFFAOYSA-N CC(CCCCCCCCOC=C)(C)C Chemical compound CC(CCCCCCCCOC=C)(C)C IOVZXONIQGYGEF-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
244000287680 Garcinia dulcis Species 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000283986 Lepus Species 0.000 description 1
101100286668 Mus musculus Irak1bp1 gene Proteins 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
241001208007 Procas Species 0.000 description 1
241001327627 Separata Species 0.000 description 1
241001302210 Sida <water flea> Species 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
150000008378 aryl ethers Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000003851 azoles Chemical class 0.000 description 1
FMGSZGVKLGVBIT-UHFFFAOYSA-N benzoic acid ethenyl acetate ethenyl benzoate Chemical compound C(C)(=O)OC=C.C(C1=CC=CC=C1)(=O)OC=C.C(C1=CC=CC=C1)(=O)O FMGSZGVKLGVBIT-UHFFFAOYSA-N 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
LUDNODSVOUWZAW-UHFFFAOYSA-N cyclohexanecarboxylic acid ethenyl acetate ethenyl cyclohexanecarboxylate Chemical compound C(C)(=O)OC=C.C1(CCCCC1)C(=O)OC=C.C1(CCCCC1)C(=O)O LUDNODSVOUWZAW-UHFFFAOYSA-N 0.000 description 1
125000004989 dicarbonyl group Chemical group 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
XCLIHDJZGPCUBT-UHFFFAOYSA-N dimethylsilanediol Chemical compound C[Si](C)(O)O XCLIHDJZGPCUBT-UHFFFAOYSA-N 0.000 description 1
NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
WGXGKXTZIQFQFO-CMDGGOBGSA-N ethenyl (e)-3-phenylprop-2-enoate Chemical compound C=COC(=O)\C=C\C1=CC=CC=C1 WGXGKXTZIQFQFO-CMDGGOBGSA-N 0.000 description 1
IGBZOHMCHDADGY-UHFFFAOYSA-N ethenyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC=C IGBZOHMCHDADGY-UHFFFAOYSA-N 0.000 description 1
WNMORWGTPVWAIB-UHFFFAOYSA-N ethenyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC=C WNMORWGTPVWAIB-UHFFFAOYSA-N 0.000 description 1
WBZPMFHFKXZDRZ-UHFFFAOYSA-N ethenyl 6,6-dimethylheptanoate Chemical compound CC(C)(C)CCCCC(=O)OC=C WBZPMFHFKXZDRZ-UHFFFAOYSA-N 0.000 description 1
TVFJAZCVMOXQRK-UHFFFAOYSA-N ethenyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OC=C TVFJAZCVMOXQRK-UHFFFAOYSA-N 0.000 description 1
ZNIJFAJFNZEXNI-UHFFFAOYSA-N ethenyl acetate ethenyl prop-2-enoate prop-2-enoic acid Chemical compound C(C)(=O)OC=C.C(C=C)(=O)OC=C.C(C=C)(=O)O ZNIJFAJFNZEXNI-UHFFFAOYSA-N 0.000 description 1
ZGBAXNVZAOWEKK-UHFFFAOYSA-N ethenyl acetate;2-ethylhexanoic acid Chemical compound CC(=O)OC=C.CCCCC(CC)C(O)=O ZGBAXNVZAOWEKK-UHFFFAOYSA-N 0.000 description 1
KEHZQFNLRUZKMO-UHFFFAOYSA-N ethenyl butanoate ethenyl 2,2-dimethylpropanoate Chemical compound C(CCC)(=O)OC=C.C(C(C)(C)C)(=O)OC=C KEHZQFNLRUZKMO-UHFFFAOYSA-N 0.000 description 1
DGEVQWMOSLUFDQ-UHFFFAOYSA-N ethenyl cyclohex-3-ene-1-carboxylate Chemical compound C=COC(=O)C1CCC=CC1 DGEVQWMOSLUFDQ-UHFFFAOYSA-N 0.000 description 1
JZRGFKQYQJKGAK-UHFFFAOYSA-N ethenyl cyclohexanecarboxylate Chemical compound C=COC(=O)C1CCCCC1 JZRGFKQYQJKGAK-UHFFFAOYSA-N 0.000 description 1
CMDXMIHZUJPRHG-UHFFFAOYSA-N ethenyl decanoate Chemical compound CCCCCCCCCC(=O)OC=C CMDXMIHZUJPRHG-UHFFFAOYSA-N 0.000 description 1
125000005670 ethenylalkyl group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
IUXQFLRZZUQUPJ-UHFFFAOYSA-N prop-1-enyl benzoate Chemical compound CC=COC(=O)C1=CC=CC=C1 IUXQFLRZZUQUPJ-UHFFFAOYSA-N 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003336 secondary aromatic amines Chemical class 0.000 description 1
150000004819 silanols Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229940070710 valerate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/04—Formic acid esters
- C07C69/10—Formic acid esters of trihydroxylic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA002075622A 1990-11-30 1991-11-27 Technologie de transvinylation assistee par un milieu azeotropique Abandoned CA2075622A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US62123890A	1990-11-30	1990-11-30
US621,238		1990-11-30

Publications (1)

Publication Number	Publication Date
CA2075622A1 true CA2075622A1 (fr)	1992-05-31

Family

ID=24489338

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002075622A Abandoned CA2075622A1 (fr)	1990-11-30	1991-11-27	Technologie de transvinylation assistee par un milieu azeotropique

Country Status (14)

Country	Link
EP (1)	EP0513331A1 (fr)
JP (1)	JPH05503948A (fr)
KR (1)	KR920703503A (fr)
AU (1)	AU9116891A (fr)
BG (1)	BG96711A (fr)
BR (1)	BR9106065A (fr)
CA (1)	CA2075622A1 (fr)
EC (1)	ECSP910793A (fr)
FI (1)	FI923416L (fr)
HU (1)	HUT63603A (fr)
MC (1)	MC2241A1 (fr)
NO (1)	NO922980L (fr)
WO (1)	WO1992009554A1 (fr)
ZA (1)	ZA919454B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2934264B1 (fr) *	2008-07-22	2012-07-20	Arkema France	Fabrication d'esters de vinyle a partir de matieres renouvelables, esters de vinyle obtenus et utilisations
DE102012002274A1 (de) *	2012-02-06	2013-08-08	Oxea Gmbh	Verfahren zur Koppelproduktion von Vinylestern und Essigsäurefolgeprodukten oder Propionsäurefolgeprodukten
DE102012002282A1 (de)	2012-02-06	2013-08-08	Oxea Gmbh	Verfahren zur Herstellung von Vinylestern
DE102013224496A1 (de)	2013-11-29	2015-06-03	Wacker Chemie Ag	Verfahren zur Ruthenium-katalysierten Umvinylierung von Carbonsäuren
DE102013224491A1 (de)	2013-11-29	2015-06-03	Wacker Chemie Ag	Verfahren zur Ruthenium-katalysierten Umvinylierung von Carbonsäuren
DE102014206916A1 (de)	2014-04-10	2015-10-15	Wacker Chemie Ag	Verfahren zur Ruthenium-katalysierten Umvinylierung von Carbonsäuren
DE102014206915A1 (de)	2014-04-10	2015-10-15	Wacker Chemie Ag	Verfahren zur Darstellung einer aktiven Ruthenium-Katalysatorlösung für die Umvinylierung von Carbonsäuren
DE102014210835A1 (de)	2014-06-06	2015-12-17	Wacker Chemie Ag	Verfahren zur Trennung von hochsiedenden Carbonsäurevinylester/Carbonsäure-Gemischen
DE102015216373A1 (de)	2015-08-27	2017-03-02	Wacker Chemie Ag	Verfahren zur katalytischen Umvinylierung von Carbonsäuren

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE912810C (de) *	1943-02-18	1954-06-03	Wacker Chemie Gmbh	Verfahren zur Herstellung von monomeren Vinylestern
DE1282014C2 (de) *	1967-01-12	1969-07-17	Hoechst Ag	Verfahren zur Gewinnung von Vinylestern und Carbonsaeuren
DE1668650A1 (de) *	1968-02-20	1971-09-23	Reichhold Albert Chemie Ag	Verfahren zur Herstellung von Estern durch Umacylieren von Estern
US3755387A (en) *	1969-08-05	1973-08-28	Dow Chemical Co	Vapor phase transvinylation process
GB1486443A (en) *	1975-05-19	1977-09-21	Ici Ltd	Production of vinyl esters of organic carboxylic acids

1991
- 1991-11-19 EC EC1991000793A patent/ECSP910793A/es unknown
- 1991-11-27 AU AU91168/91A patent/AU9116891A/en not_active Abandoned
- 1991-11-27 KR KR1019920701790A patent/KR920703503A/ko not_active Withdrawn
- 1991-11-27 MC MC91US9108757D patent/MC2241A1/fr unknown
- 1991-11-27 EP EP92901814A patent/EP0513331A1/fr not_active Withdrawn
- 1991-11-27 HU HU922264A patent/HUT63603A/hu unknown
- 1991-11-27 CA CA002075622A patent/CA2075622A1/fr not_active Abandoned
- 1991-11-27 WO PCT/US1991/008757 patent/WO1992009554A1/fr not_active Ceased
- 1991-11-27 BR BR919106065A patent/BR9106065A/pt not_active Application Discontinuation
- 1991-11-27 JP JP4501986A patent/JPH05503948A/ja active Pending
- 1991-11-27 FI FI923416A patent/FI923416L/fi unknown
- 1991-11-29 ZA ZA919454A patent/ZA919454B/xx unknown
1992
- 1992-07-28 NO NO92922980A patent/NO922980L/no unknown
- 1992-07-29 BG BG096711A patent/BG96711A/bg unknown

Also Published As

Publication number	Publication date
BG96711A (bg)	1993-12-24
KR920703503A (ko)	1992-12-18
HUT63603A (en)	1993-09-28
BR9106065A (pt)	1993-03-09
MC2241A1 (fr)	1993-02-23
FI923416A0 (fi)	1992-07-29
AU9116891A (en)	1992-06-25
WO1992009554A1 (fr)	1992-06-11
EP0513331A1 (fr)	1992-11-19
JPH05503948A (ja)	1993-06-24
ZA919454B (en)	1992-09-30
NO922980L (no)	1992-09-18
NO922980D0 (no)	1992-07-28
FI923416A7 (fi)	1992-07-29
FI923416L (fi)	1992-07-29
ECSP910793A (es)	1992-12-21

Publication	Publication Date	Title
KR100408144B1 (ko)	2004-03-30	카보닐화공정동안형성된희석수성스트림으로부터아세트산을회수하는방법
KR100192733B1 (ko)	1999-06-15	카보닐화 스트림으로부터 카보닐 불순물을 제거하는 방법
US4311851A (en)	1982-01-19	Preparation of carboxylic acid esters with BF3 -alcohol complex catalyst
JP2009073846A (ja)	2009-04-09	カルボニル化生成物の回収方法
MC2036A1 (fr)	1990-05-30	Procede de transvinylation
CA2060398C (fr)	1997-07-15	Procede de transvinylation par distillation reactive
KR100762773B1 (ko)	2007-10-04	연속식 에틸 락테이트 제조 방법
JPH04330063A (ja)	1992-11-18	アルキルイミダゾリドン（メタ）アクリレートの製造方法
KR100591625B1 (ko)	2006-06-21	포름 알데히드 함유 혼합물의 처리
CA2075622A1 (fr)	1992-05-31	Technologie de transvinylation assistee par un milieu azeotropique
RU2203264C2 (ru)	2003-04-27	Способ получения уксусной кислоты
EP0210907B1 (fr)	1989-09-13	Procédé de préparation d'esters méthacryliques par transestérification
KR100452078B1 (ko)	2004-11-16	알칸올에의한(메트)아크릴산의에스테르화방법
US6008404A (en)	1999-12-28	Acrylate monomer preparation using alkali metal alkoxides as ester interchange catalysts and bromide salt polymerization inhibitors
JP3502523B2 (ja)	2004-03-02	アルキルハロゲン化物の連続的な製法
EP0017441B2 (fr)	1987-10-28	Préparation d'esters
JP2943523B2 (ja)	1999-08-30	アクリル酸エステルのミカエル付加物から有用化合物を製造する方法
JP2861983B2 (ja)	1999-02-24	アクリル酸エステルのミカエル付加物の分解方法
JP3238894B2 (ja)	2001-12-17	メタクリル酸メチルの製造方法
GB2199030A (en)	1988-06-29	Process for preparing ox-phenylpropionie acid
JPS60258142A (ja)	1985-12-20	安息香酸の精製法
US9822059B2 (en)	2017-11-21	Method for separating high-boiling carboxylic acid vinyl ester/carboxylic acid mixtures
JPH01502748A (ja)	1989-09-21	腐食の発生を抑制したメチル第３級アルキルエーテルの合成法
FR2838434A1 (fr)	2003-10-17	Procede de fabrication de l'acrylate de butyle par esterification directe
US4297505A (en)	1981-10-27	Process for the preparation of pentachloro-3-butenoic acid esters

Legal Events

Date	Code	Title	Description
1992-07-30	EEER	Examination request
1995-05-27	FZDE	Discontinued